Generation and reactions of a selenoamide dianion

被引：26

作者：

Murai, T ^{[1
]}

Aso, H ^{[1
]}

Kato, S ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 08期

关键词：

D O I：

10.1021/ol0257629

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The selective generation of selenoamide monoanion and dianion was achieved by reacting N-benzyl selenobenzamide with BuLi. Alkylation of the dianion with 1 equiv of electrophile took place at the carbon atom adjacent to the nitrogen atom, and subsequent hydrolysis produced functionalized selenoamides in good to high yields. Ring opening of oxiranes using the dianion proceeded with high regio- and stereoselectivity to form N-3-hydroxy-1-phenylalkyl selenobenzamides. The stereochemistry of the major isomer derived from cyclohexene oxide was determined by X-ray molecular structure analysis.

引用

页码：1407 / 1409

页数：3

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